Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

74155

Sigma-Aldrich

Nonactin

from Streptomyces sp., ≥97.0% (TLC)

Synonym(s):

Ammonium ionophore

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C40H64O12
CAS Number:
6833-84-7
Molecular Weight:
736.93
Beilstein/REAXYS Number:
76434
EC Number:
229-911-3
UNSPSC Code:
51102829
PubChem Substance ID:
24886652
NACRES:
NA.85

biological source

Streptomyces sp.

Quality Level

200

assay

≥97.0% (TLC)

form

powder

color

white to faint yellow

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes
cell membrane | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

C[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](C)C[C@H]3CC[C@H](O3)[C@H](C)C(=O)O[C@@H](C)C[C@@H]4CC[C@@H](O4)[C@@H](C)C(=O)O[C@H](C)C[C@H]5CC[C@H](O5)[C@H](C)C(=O)O1

InChI

1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-

InChI key

RMIXHJPMNBXMBU-QIIXEHPYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Chemical structure: macrolide
May contain the homologues monactin and dinactin

Application

Nonactin is used as a neutral lipid membrane soluble ammonium (and potassium) ionophore, as an uncoupler of oxidative phosphorylation, and to inhibit surface expression of certain heat shock proteins (HSP60) [1][2].

Biochem/physiol Actions

Nonactin is a macrotetrolide that forms complexes with alkali cations, such as potassium and sodium. Nonactin has been reported to inhibit the processing of cytoplasmic precursor proteins destined for the mitochondria. Nonactin is a uncoupler of oxidative phosphorylation [3].

Packaging

5 mg

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas.Moisturesensitive. Keep in a dry place.
Natural macrotetrolide

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBR6659V
BCBP9183V
1431469V
1431469

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
Tetrahedron, 52, 571-571 (1996)
[Macrotetrolides].
W Keller-Schierlein et al.
Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles, 26, 161-189 (1968-01-01)
Sergey M Korotkov et al.
Journal of biochemical and molecular toxicology, 21(2), 81-91 (2007-04-12)
The effects of Tl(+) ions on isolated rat liver mitochondria were studied in the presence of nonactin, a cyclic ionophore. Nonenergized rat liver mitochondria were increasingly swollen at an elevated concentration of Tl(+) in the 160 mOsm medium containing 0-150
Jasmina Nikodinovic et al.
Organic letters, 8(3), 443-445 (2006-01-27)
[reaction: see text]. An efficient resolution of methyl nonactate is reported by biotransformation in shake flask cultures of Rhodococcus erythropolis. The equilibrium of the reaction redox system can be manipulated by switching from aerobic to anaerobic growth, thereby generating both
Richard J P Cannell et al.
Methods in molecular biology (Clifton, N.J.), 864, 473-514 (2012-03-01)
Follow-up of natural products isolation refers to re-isolation of compound(s) of interest in larger amounts for further pharmacological testing, conclusive structure elucidation, structure modifications to synthesize analogs for structure-activity relationships (SAR) studies, preformulation and formulation studies or clinical trials. In
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service